Herbicidal 5-oxo-imidazolinyl benzoic acids, esters and salts, their preparation and use are disclosed in U.S. Pat. No. 4,188,487 and U.S. Pat. No. 4,297,128 and pending applications for United States Patents Ser. Nos.: 823,863 01/29/86, cont. of 579,224, 02/10/84, abandoned; 631,283, 07/16/84, U.S. Pat. No. 4,554,013; Ser. No. 629/296, 07/09/84; 382,041, 05/25/82, U.S. Pat. No. 4,638,068; Ser. No. 616,747, 06/04/84, U.S. Pat. No. 4,647,301.
The free acids of these compounds may be represented in general by Formula I below ##STR1## wherein A is CR.sub.3 or N;
R.sub.1 and R.sub.2 each represent C.sub.1 -C.sub.3 alkyl or cyclopropyl, with the proviso that the sum of the number of carbon atoms in R.sub.1 and R.sub.2 is 2 to 5; and when R.sub.1 and R.sub.2 are taken together with the carbon to which they are attached, they may form a C.sub.3 -C.sub.6 cycloalkyl ring optionally substituted with methyl; PA0 X is hydrogen, halogen or methyl; PA0 Y and Z are each hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.4 alkylthio, phenoxy, C.sub.1 -C.sub.4 haloalkyl, OCF.sub.2 CHF.sub.2, OCF.sub.3, OCHF.sub.2, nitro, cyano, C.sub.1 -C.sub.4 alkylsulfonyl, NR.sub.4 R.sub.5 ; C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenyl optionally substituted with one or two C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen or combinations of any two of these groups; PA0 R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkoxy, CF.sub.3, NO.sub.2, OCF.sub.3, OCHF.sub.2 or OCF.sub.2 CHF.sub.2 ; PA0 R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; PA0 and, when taken together, Y and Z may form a ring in which YZ is represented by PA0 the N-oxides thereof when A is N provided that Y or Z cannot be alkylamino, dialkylamino or alkylthio; PA0 the optical isomers thereof when R.sub.1 and R.sub.2 are not the same; PA0 the tautomers thereof; and PA0 the acid addition salts thereof.
R.sub.5 is C.sub.1 -C.sub.4 alkyl;
(1) the structure: --(CH.sub.2).sub.n --, where n is an integer of 2, 3 or 4; or PA1 (2) by the structure: ##STR2## L, M, Q and R.sub.7 are each hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkyl, difluoromethoxy, trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy, NO.sub.2, CN, phenyl, phenoxy, amino, C.sub.1 -C.sub.4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, phenoxy substituted with one Cl, CF.sub.3, NO.sub.2 or CH.sub.3 group, C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, or C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens;
Preparation of the above-identified formula I N-oxides can be achieved following the procedures described in European Patent Application Number 81103638.3, publication number 0,041,623, incorporated herein by reference thereof.
It is an object of this invention to provide a novel process for the preparation of herbicidal imidazolinyl benzoic, nicotinic and quinoline-3-carboxylic acids of Formula I and the herbicidal esters and salts of these acids.